


Your Tomboy Friend Almost Loses Pool Game Against Two Horny College Boys

by HomerSoc



Category: Original Work
Genre: F/M, Friends to Lovers, Impregnation, Loss of Virginity, Tomboy, gwa, script offer
Language: English
Status: Completed
Published: 2021-01-18
Updated: 2021-01-18
Packaged: 2021-03-16 21:14:54
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,520
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28837632
Author URL: https://archiveofourown.org/users/HomerSoc/pseuds/HomerSoc
Summary: When two spoiled rich college boys challenge her and her male best friend to play pool for money at the bar, she agrees. She and her friend easily beat them the first two games. In the third, the college kids put down a ton of money as their wager. She says they can't cover that, but then they tell her what she can bet to match the money they put in.Eager to teach these two a lesson, she accepts over the objections of her friend. Then she proceeds to almost throw the match. Only some great shots by her friend save her from having to have sex on the pool table with the two college guys.Now the tomboy and her friend are back in the apartment, and splitting up their winnings. But there's only one problem.Her body is part of the winnings.
Kudos: 26





	Your Tomboy Friend Almost Loses Pool Game Against Two Horny College Boys

Thanks for saving my ass back there. Literally. My pussy too, since if they won that last game, those two rich college kids said they were going to double-team me on that back room pool table.

Yeah, I would have done it. A bet’s a bet. When you sunk that impossible shot, I sure as hell grabbed their money before we left. And I would have paid up had we lost. I can’t say I would have been wild about any of it. Not about losing the game to those guys, or about what I was having to do with them. Maybe it would have taught my mouth to stop writing checks my ass can’t cash. Or that my ass has to cash, I guess. 

But we won. Or you won. I somehow managed to suck during that last game. I’m usually good under pressure. But that was a lot of money if we won. If we lost, we’d have lost the money you put up for the first game, and then of course I would have had to fuck them. 

No, dude. None of this is your fault, and it’s because of you that it worked out for us. We beat their asses in two games. Then they plopped down a ton of money on a third. Seriously, who carries that kind of cash on them to a bar? Apparently these guys. They had to know we wouldn’t have nearly that much, even after winning the money for the first two games.

It’s not like they were trying to hustle us. They just wanted a rematch, and we were planning on taking the money from the first two games and leaving. But then that money came out, and we both said we couldn’t cover it. And that’s when they said I could put my body up for ante.

What is it about me that makes guys go “Yeah, I want to fuck her?” It’s got to be some tomboy fetish thing. There were plenty of other girls in that bar tonight, some actively trying to get laid. Girls with long pretty hair, or wearing dresses and perfume. It can’t have been my shampoo or deodorant, because I just use the same brand as you. And no offense, the guys ain’t hitting on you all of the time.

Anyway, they said that the money we had won so far plus my body would cover our side of the bet. You said no, but I said hell yes, because I didn’t like these guys at all and wanted to kick their asses again. Plus that was a crazy amount of money for one game of pool..

You threatened just to leave so the game couldn’t happen, so I said I would just take them on by myself. Which was what was going to happen if I lost anyway. You didn’t like the idea of leaving me alone with them, or maybe you just knew I would start to choke. Besides, part of the bet was that they wanted to make my boyfriend watch. 

They meant you of course. I’m not sure why everyone thinks we’re a couple. Just because we’ve been friends forever, and roommates since we graduated. Well, and that we seem to do everything together, other than boyfriend and girlfriend stuff, of course.

Anyway, back to the choking thing. That did happen. Part of it were their comments, reminding me of what was gonna happen if we lost. But I also kind of felt like I had put you on the spot. If we lost, you’d feel bad about what happened to me, just because you’re a good friend, and it’s kind of your thing to protect me from myself. I was worried if we did lose, you’d try to pick a fight with those guys. While I’d have loved to kick their asses with you, as I said, a bet’s a bet. I’d have to convince you not only to not try to beat the hell out of them, but also to stay and watch as they claimed their prize.

So I missed a key shot or two. They weren’t playing their best either. As it looked more and more like they might win, they got more distracted. That’s how you were able to run the table there at the end, including that awesome eight ball banked into the corner pocket.

But we’re all good now. We’re back at the apartment, instead of me being part of a tomboy sandwich on that pool table. And we have all of this money. Just look at it!

No, I’m not going to keep all of it. Don’t tell me that. We’re a team. You were the one who fronted the money for us for the first two games, and then the person that won the third. I just bet my body there in the last game. So we are going to split the pot evenly. Plus returning your original bet on top of that of course. We could cover a few rent payments with the money. I was thinking of maybe even getting a PS5 and some games. But really, do with your money what you want.

So that takes care of splitting the money portion. But there’s still the rest.

Yeah, the rest of the pot. There was money at stake. But there was also my body. Did you forget that? We basically get to split what I was offering those two dickheads.

Anyway, I was thinking I would call dibs on the ass part, although I wasn’t going to do anything with that. Well, other than normal day to day ass stuff. I could explain more, but I’m guessing you don’t want to hear that, and I gotta preserve the whole tomboy feminine mystique thing.

That leaves you with my pussy. Well, at least the use of it once. 

No, I’m not joking. Would I mess with you? Well, other than maybe shaving off your eyebrows that one time, or replacing your toothpaste with mayonnaise, or… okay, so I would mess with you. But not on this.

Like I said, a bet is a bet. If I was willing to bone those two guys over the bet, then that’s part of the pot still. And you’re entitled to half of it. Guys apparently have this weird obsession with me and doing sexual things to me, so I got to thinking that maybe you weren’t any different and would want a go. By winning that game for us, you’ve earned that from your winnings.

It’s okay if you do. Honestly, the way that last game was going, I had kind of resigned myself to being banged in both holes by those guys, and I really hated them. You’re my best friend though. I wouldn’t mind taking it in the one hole from you nearly as much. And like I’ve been saying, I always pay my debts.

You could say no. Doesn’t really make much sense if you do though. Like I said, guys always seem to have a thing for me. Maybe you do too, and you’re just too good of a friend to be obvious about it. Guys always seem to be thinking about sex anyway, and always trying to have it when they can.

If you don’t, then I suppose I need to give you more of the money we won. But that means putting a price on sex with me. I’m not really comfortable with that in general, or in coming up with a specific price for it. That was part of what annoyed me when they said my body could cover our side of the bet. I didn’t like having a value assigned to me like that.

So, do you want to put a price on sex with me?

[laugh] I thought not. My best bud isn’t that dumb. Or that much of a dick, either.

Well, the only way this works out smoothly is if we split the money, and then you take your fair share of my body, too. Whether you do it or not, I’d keep feeling like I owed it to you, and that’s just going to keep gnawing away at me. It might even get in the way of our friendship.

Maybe it’s a bad idea. But I’ve already made so many bad calls tonight, what’s one more? You saved me from the other ones, and something tells me you’ll keep this one from getting out of control too. It’s just some sex, and nothing more than that. We know each other better than that.

But, maybe it wouldn’t hurt, just this once, to get to know each other a little better?

I’ll take off this jacket. I never took it off at the bar because it’s just a t-shirt on underneath and nothing under that. I hate bras, but I’m not fond of the attention not wearing one tends to get me either. Not that the jacket kept those two guys from noticing me. But now that the jacket is off, you’ll notice that I’m more than tomboy. Sure, I wear this around you a lot, but now I’ve put all kinds of ideas in your head. Now that I think about, you’ve avoided staring at me too much when I do that. Or more specifically, certain parts of me. So i guess you were aware of my body before then. Well, now you can look to your heart’s content.

I’ll take off the jeans too. I don’t go for as tight as other girls wear them, but from the comments I get some people, apparently I still make them look good. It’s like everything I do to not be feminine just makes me sexier to some people. I do wear panties underneath, just because I like how they stay closer to my skin than boxers or briefs, but other than that, it’s my main nod to femininity. 

Well, your turn. You get down to your underwear too, and then once you’re wearing as little as me, we can take off the rest. For you, it means losing that shirt. I like that shirt, actually. I know I’ve said that. I’d kind of like to borrow it sometime, except then people might get the wrong idea. They might think we do what we’re building up to do right now.

Except they seem to think it anyway. They just think I watch you undress all of the time. Just because we’ve always hung around together and now live together doesn’t mean anything. We’re gonna have sex only because of the pool game tonight. Not anything else.

Okay, now you’re just wearing your underwear. You’re actually wearing less than me, since I still have this shirt on, although you can kind of see my nipples through it. Then again, I can see something poking against your boxers, so this underwear isn’t really giving us much modesty. And when I take off this shirt… well, I have even less.

It’s okay. You can look at them. I don’t recall you seeing them before. Maybe a glance down my t-shirt or something if I was being careless. But not a good, full on view like this. I’m not proud to say it, but towards the end of that last game I was trying to distract those guys with them.

So, do you like them?

It’s okay if you do. It’s even okay to say you do. Right now at least. I wouldn’t mind some comments on my body that didn’t come from some drunken college boys. 

[pause for reply]

Thanks. For what it’s worth, you look kinda good without much clothing on, too. Not that I’m much of a judge of bodies, since I don’t get why men seem to always think mine is special. But yours seems pretty nice. Like I’d choose you for my avatar in a video game.

So, um, I guess we should take off the rest? Maybe at the same time? Then it’s less like one of us is stripping for the other, and more efficient anyway.

There. My panties are off, and your boxers. Your, um, pool stick is very prominent at the moment. Which is good of course, if we’re going to have sex. I was thinking we could do it out here in the living room. It won’t be as comfortable as a bed, but anything would be better than the pool table things were kind of leading up to. Plus the living room is neutral territory in this apartment. It’s like Switzerland, minus the cheese and the cool army knives. I need to get me another one of them. Or another multi-tool, or-

Sorry. I was going off on a tomboy tangent there. But we could have sex here in the living room. And maybe I could be on top. I realize I’m your prize, but I think you’ll enjoy this no matter what position we’re in. I kind of like the feeling of being a bit more in control of things, which I’ll get by sitting on top of you as you lie down. It will definitely beat being stuck between those two other guys tonight. 

Wow. Didn’t take you long to lie down on the floor, did it? [laugh] You are kind of looking forward to this. I’m glad I didn’t let you weasel out of your winnings. Those college kids wouldn’t have given up their claim, just like I grabbed the money when you sunk that last shot.

Well, that game-winning shot earns you a shot at me. Except instead of sinking a ball in a pocket, you’ll be sinking your cock into my pussy. At least, you will be once I step over you, and then sink down slowly onto my knees. As I hover over you and your cock, I guess you’re getting a good look at my chest from that angle. My face too, if you’re into tomboys like pretty much every guy I run into seems to be. It’s okay to be into me tonight though. Because pretty soon you’re going to be in me.

They way that things sticking up, I think I could just lower myself straight down and have it go right in. But let’s do this right. I’ll grab onto it with my hand and hold it there. [laugh] it jumps as my hand goes around it. Haven’t been touched by anyone other than you for a while I’m guessing. In fact, I’m pretty sure that’s it. Then I just hold it in place, and lower myself down a bit until it’s like we’re about to chalk your stick up for a tricky shot. Except this one won’t be that hard to make. Between you being so hard, and me being wet for some reason, I don’t think this will require much skill at all. At least to get it in. But maybe put your hands on my hips to help balance me. Yeah, like that. Don’t be shy. We’re a little beyond that now.

You ready? Kind of a dumb question, because obviously you are. Maybe I was asking myself. But don’t worry. I know what I’m doing. Even if maybe I’ve never done it before.

Now, before you can figure out what I mean by that, I’m going to lower myself and…

[moan as entered]

Oh fuck. That’ll sober you up. Not that either of us were that drunk. We just had a couple of beers over a few hours of playing pool. It’s not a bad experience either. Especially since it’s my best friend’s cock, instead of two cocks from two snotty college kids at the same time. I’d be enjoying that a lot less, especially if you had to watch. 

But it’s okay to watch me now. Watch as I slowly move up and down on your cock. My pussy clings to it so tightly, but I can still move up and down pretty good, all while I look down into your face. You’re enjoying this a suspicious amount, dude. Are you into me or something?

[laugh] Just messing with you dude. If I can’t fuck with my best friend while I’m fucking him, then what fun is that? Of course you’re enjoying it as your tomboy best friend leisurely rides your cock. Men seem to enjoy the idea of sex with any girl, and with me specifically. Well, you’re the only one who has gotten me. Those two guys almost did, except you saved me. And I’m going to show a good bit more enthusiasm for you then I would have for them. I didn’t even say anything about a condom, because taking me barebacked was part of their bet. 

Mmm. This is starting to feel pretty good. I know you won’t mind if I start moving around a little more. Not just faster, but also moving back and forth and not just up and down. Really, any kind of direction I can make work.

But yeah, this could have been a really messed-up evening. One of those guys could have impregnated me. Maybe the odds are against it, just like it doesn’t mean I’ll get pregnant if you cum in me. But I owe you everything they were gonna get if they won. Except the paternity suit I would have slapped them with if I would have gotten preggers.

But don’t worry about that. I wouldn’t sue you. Don’t even worry about getting me pregnant. I’m not. Not right now at least. If it’s your kid, it doesn’t seem too bad to have it in me. Maybe ‘cause your cock feels so good to have in me right now. Well, in and out of me, again and again.

Keep holding onto my hips. I’m going to lean over towards you now and support myself with my hands. I think I can get some really good leverage then.

[soft moan] See? Now we’re talking. And now you have to put up with my face closer to yours. I hope you don’t mind. Not close enough where you can make this weird by kissing me while we do it. But close enough for us to see every expression on the other’s face, and look dangerously into each other’s eyes. 

They would have just fucked me on that pool table. One on each hole, like they said. Maybe they would changed sides at halftime. At some point they would have left me leaking cum on that table, and we would have had an awkward ride back home.

This is so much better, isn’t it? The only cum in me is gonna be yours, and coming out of the right hole, too. And no awkward ride, because we’re already home. There’s no reason this has to be awkward at all afterward. Even if you do knock me up. But it’s not like there will be any other consequences of our having fucked just once. 

You’re going to cum soon, aren’t you? I’m pretty sure I’m going to. Unless you finish real soon, but you seem kind of like the type that would make the effort to wait for a girl. And I am so close. It’s not like I would have come for them. At least I hope not. But I will cum for you, and without any regret. Then we just act like it never happened, and everything is cool.

But that’s later. Our now is that we’re about to cum, and I want to cum together. I want to feel you cum in me as I’m losing control myself. I’m not being a very good tomboy right now. I feel like I should burp or talk sports or something. But all I can think about is bouncing on your cock, and looking at your face and your stupid eyes. 

Oh fuck. I don’t think I can wait much longer. Don’t let me cum before you. We need to do it together. So you better hurry. I’m trying to fight it, but I can’t anymore. But you can’t either. Neither of us wants to fight any of this anymore. So please.. Cum in me…

I’m cumming! And you are too. I can see it in your face, and feel it in my pussy…

[orgasm]

[pause]

Well, that was more fun than I expected. And more exhausting. I’m just going to lie down beside you here for a few minutes. At least if you don’t mind. Not cuddling or anything like that, of course. Just me lying down next to you, and somewhat against you.

Thanks for that. For saving my ass tonight, of course. But also for the sex. It turned out to be a little more fulfilling than just sharing our winnings tonight.

The way you enjoyed it, and the way you looked at my body though… I guess I can maybe understand why guys are attracted to me. It still doesn’t excuse them being dicks about it though.

And that other thing. About people always assuming we’re some kind of couple? 

Maybe they weren’t so crazy after all...


End file.
